Chloromethyl Methyl Ether → HCID 14600606, compound

HRID 2107020Notes

Reaction equation

HRID 2107020 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[CH:6][CH:5]=1.[CH3:19][O:20][CH2:21]Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:19][O:20][CH2:21][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 14600605HCID 14600605, compound

Product 1

HCID 14600606HCID 14600606, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension comprising 1.0 g of sodium hydride in 40 ml of dry tetrahydrofuran, 5.27 g of 8-(4-hydroxyphenyl)octanol dissolved in 50 ml of dry tetrahydrofuran was added dropwise at 0° C. The resulting mixture was stirred at room temperature for 30 minutes and then cooled to 0° C. again. Subsequently, 2.1 ml of chloromethyl methyl ether was added dropwise thereto. After stirring at room temperature for 30 minutes, the mixture was cooled to 0° C. and ice and a saturated aqueous solution of sodium bicarbonate were added thereto. The resulting mixture was then extracted with ethyl acetate. The extract was concentrated and subjected to column chromatography (silica gel, ethyl acetate: hexane=1:3-1:2). As a result, 4.05 g of the desired compound was obtained (yield: 66%).

Workup

  1. additionwas added dropwise at 0° C
  2. temperaturecooled to 0° C. again
  3. stirringAfter stirring at room temperature for 30 minutes
  4. temperaturethe mixture was cooled to 0° C.
  5. extractionThe resulting mixture was then extracted with ethyl acetate
  6. concentrationThe extract was concentrated

Sources & evidence

ORD record
ord-4414def337cc436bb5c749f98dd1465c
Source dataset
uspto-grants-1990_06
Patent number
US04933329

Reaction notes

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